Learning from Great Leaders — Building a Business

By Cindy Bertram

Over the years I’ve run across great leaders in diverse industries. Ones in the travel industry have been truly inspiring, and I’ve been fortunate to get to know several of them through my work. I’ve learned so much — how they lead people, their own work styles, what’s important to them, how they interact on a day to day basis and more. Learning from them has helped me build my leadership style, and this ties directly into my work style. Having a great leadership style is the best way to successfully build our own businesses. 


Herb Kelleher, visionary co-founder of Southwest Airlines

Herb Kelleher, the co-founder of Southwest Airlines is one person I grew to admire so much over the years. Herb was actually San Antonio lawyer, and in 1966 he met with Rollin King at the St. Anthony’s Club. Rollin reached out to Herb because he had an idea of starting a low-fare airline in Texas. They actually sketched out the rough idea for Southwest Airlines on a cocktail napkin. It’s a fun story because you don’t often hear of two men creating a phenomenally successful business that way. 

After Herb successfully won a court case in 1971, Southwest Airlines began operating in Texas. Other airlines wanted to shut them down even before they started. During his first ten years, Herb, who was Southwest Airline’s lawyer and board member, spend the majority of his time defending Southwest Airlines against lawsuits from different airlines. They made it through, and Southwest Airlines turned its first profit in 1973. Herb became Chairman of Southwest Airlines in 1978, and then became CEO in 1982. 

Connecting with Herb

Herb Kelleher was featured as the front cover story for the May 28, 2001 edition of FORTUNE. He was getting ready to step down as CEO and President of Southwest Airlines, but was going to remain on as Chairman. His phenomenal personality shined and I decided to send him a personal letter. In my letter I mentioned his leadership style inspired me, and that the people who worked at Southwest Airlines were always so great to work with. I also shared an actual story of a Southwest Airlines employee who went “above and beyond” helping one of my clients.

Herb responded back to me, and in his letter dated June 28, 2001, he first said, “You flatter and humble me with your praise, but the credit for the success of Southwest Airlines goes to our magnificent Employees.” He shared a few more thoughts and then ended saying, “Thank you for writing, and we look forward to many more years of serving our mutual Customers.”

Later in July 2001, I reached out to Herb Kelleher again, but this time it was to get a quote from him to use in a travel industry related column I was writing. Herb responded back to me again, and in his letter dated August 6, 2001, he gave me a wonderful story and paragraph sharing his thoughts on that topic and analogy. He then ended his letter saying, “Thank you for wanting to include my thoughts in your column.”

What also impressed me about Southwest Airlines surfaced after the tragedies of 9/11. It wasn’t an easy time, and a challenge that hurt the travel industry. And while other major airlines were trying to get bailout money from our Federal government? Southwest Airlines didn’t. They also made sure that none of their employees lost their jobs.

Herb’s work style and leadership

Herb’s two letters to me in a short time displayed one example of his work and leadership style. He was accessible, and he truly cared. At Southwest Airlines he had created a “culture of commitment.” He wanted to make sure his employees came first, because he felt happy employees would lead to happy customers. Herb was known for inviting employees to a weekly Friday cookout, and handling baggage during Thanksgiving rush. He would show up at company gatherings, riding in on a Harley-Davidson motorcycle, sometimes dressed as Elvis, and singing “Blue Suede Shoes.”

In his 30+ years holding top executive roles at Southwest Airlines, Herb’s focus on their employees at Southwest Airlines has been a core part of what has made Southwest Airlines continue to be so successful today. Although Herb recently passed away January 3, 2019, his legend will continue to live on. The employees at Southwest Airlines continue to be the core of Southwest Airlines’ success.

Another great leader — Richard “Rick” Sasso, Chairman of MSC Cruises (USA) Inc.

I’ve been fortunate to know Richard “Rick” Sasso, Chairman of MSC Cruises (USA) Inc. since the late 1980’s. I first got to know Rick when he was Vice-President of another cruise line. After first getting to know Rick, I would write him if something came up and he’d get right back to me. When emails became an easier way for us to communicate? Rick’s fast turnaround responding back to me was even faster. And it’s been a core of his management and leadership style. A key part of his leadership style — Rick is very accessible, he genuinely cares, and he leads by example.

Rick has been one of my mentors, and someone I greatly admire. He has continued to encourage me. After going through a tough situation last year, Rick sent me an email and said, “First and foremost, the only real item is and always will be, NEVER GIVE UP Cindy.” 

Rick and I have also had a discussion about luck. As far as being lucky, Rick said, “You hear people say, ‘I was lucky.’ What they should have understood is that it is only luck if you don’t deserve the reward. But if you make decisions that eventually gave you a lucky opportunity, then you made that luck. So you have to make luck. And this comes in many forms of action.”

Over the past few years, MSC Cruises USA has been working hard to build their presence in the North American cruise market and grow the number of travel professionals who work with them. Rick explained, ‘It’s about the human factor. There is a people connection and we’re continuing to take that to the next level.” Another point Rick made was, “In business, you need executives in each touch point to have a happy guest.”

Rick is well known for his hands-on approach and this is where he truly stands out as a genuine leader who cares. 

Richard “Rick” Sasso, Chairman of MSC Cruises (USA) Inc.

Richard “Rick” Sasso, Chairman of MSC Cruises (USA) Inc.

Sister Jean, Chaplin, who inspired Loyola Ramblers and seen on national news An inspirational woman who became a household name in the spring of 2018 was Sister Jean Dolores Schmidt, Chaplain for the Loyola University Chicago Loyola Ramblers. Known as Sister Jean, she has served as Chaplain since 1994. During her career in different areas of education that includes both teaching and advising, she has mentored both young men and women. When the Loyola Ramblers moved into being one of final 16 teams in the NCAA finals and then proceeding into the Final Four, Sister Jean was there providing inspiration, with her charisma, smiles and pregame prayers and pep talks.When I had a chance to interview Sister Jean to include her in a book I was writing, we covered several diverse areas. The topic of leadership came up and I asked her what she has shared with others. Being a mentor and leader herself, I asked her what people should do when it came to pushing forward, achieving a goal and never giving up. Sister Jean explained, “It’s really about people. Leaders have to believe they are leaders and they have a plan, have a direction, lead the people and share information and communicate.”
Traits of good leadersTake a look at the wonderful leaders whose expertise ranges from the travel and cruise industries along other areas, and you’ll see key traits that these people have and share. Here are some key ones.

  • Have a hands-on approach 
  • Lead by example
  • Employees are at the core of success
  • Have a fast turnaround mindset 
  • Get back to people in a timely way
  • Create your own opportunities and make decisions that create your own “luck”
  • Focus on the human factor
  • Continue learning and growing
  • Have touch points with your clients
  • Make interactions personal, and remember that people are not machines
  • Create a fun factor 
  • Final Thoughts
  • In a world that has challenges and tragedies, it’s also critical to have a fun factor. When I heard about Herb Kelleher riding into company gatherings on a Harley-Davidson motorcycle, sometimes dressed as Elvis and singing “Blue Suede Shoes,” I thought, this created a fun difference!
  • Sister Jean’s amazing energy as a very active 99 year old, also has created a fun factor to the Loyola Ramblers’ games. 

And Rick Sasso’s work in the cruise industry for over 30 years showcases his core of being a real person, making sure guests on cruise ships enjoy, have fun, embrace their unique experiences and relax. As travel professionals, our own leadership skills are a part of how we create our own successes. And for me, focusing on making decisions that create successes and my own luck is one. Another is making sure that I also focus on the fun parts is what I’m doing. Travel does that!

Sister Jean, Chaplin,  and  Cindy Bertram

Sister Jean, Chaplin, and Cindy Bertram